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  • Title: Derivatives of 16alpha-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: synthesis and gas chromatography/mass spectrometry analysis.
    Author: Pouzar V, Cerný I, Hill M, Bicíková M, Hampl R.
    Journal: Steroids; 2005 Oct; 70(11):739-49. PubMed ID: 15913684.
    Abstract:
    Derivatives of 16alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3beta,16alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by l-Selectride or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7alpha-hydroxy and 7beta-hydroxy derivatives of 16alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by (1)H and (13)C NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods.
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